Acetic Anhydride → 2-Chloro-3-nitro-6-acetoxymethylpyridine
Reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N+:3]=1[O-].[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14]>>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH2:11][O:16][C:13](=[O:15])[CH3:14])[N:3]=1Participants
Conditions
- Temperature
- 60 °C
Procedure
2-Chloro-3-nitro-6-picoline-N-oxide (1,6 g, 8.5 mmol) was dissolved in acetic anhydride (5 mL) and the solution was heated in a 60° C. oil bath for 3 hours. The solvents were removed under vacuum and the dark residue was partitioned between methylene chloride (30 mL) and saturated aqueous potassium carbonate (100 mL). The aqueous layer was re-extracted with more methylene chloride (2×40 mL) and the combined methylene chloride layers were dried with magnesium sulfate, filtered and evaporated under vacuum. The crude solid was dissolved in methylene chloride (SmL) and was loaded onto a silica gel column (E. Merck 60, 230-400 mesh, 2.5×24 cm). The column was eluted with methylene chloride collecting 8 mL fractions. Fractions 11-26 were combined and evaporated to give the title compound (0.42 g) as a white solid.
Workup
- customThe solvents were removed under vacuum
- customthe dark residue was partitioned between methylene chloride (30 mL) and saturated aqueous potassium carbonate (100 mL)
- extractionThe aqueous layer was re-extracted with more methylene chloride (2×40 mL)
- dry with materialthe combined methylene chloride layers were dried with magnesium sulfate
- filtrationfiltered
- customevaporated under vacuum
- dissolutionThe crude solid was dissolved in methylene chloride (SmL)
- washThe column was eluted with methylene chloride collecting 8 mL fractions
- customevaporated
Sources & evidence
- ORD record
- ord-410ce3bbfe464423adcedbfbc5a627d6
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05565445
Reaction notes
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